Reclaim.ai
2024
Why
Added AI scheduling and calendar-management tools to support Dropbox's AI work strategy.
Dropbox, Inc.
Cloud Storage and Collaboration SoftwareFounded 2007- HQ today: San Francisco, California
Reviewed by Swet Parvadiya
Company data updated: October 2026
Acquisitions
Dropbox Acquisitions
6
Major Deals Covered
$490M
Disclosed Deal Value
What are Dropbox's biggest acquisitions?
Dropbox's largest disclosed acquisition here is HelloSign for $230M in 2019. This page covers 6 major deals from 2013 to 2024, each with its price where disclosed and the reason behind it.
- Major deals covered
- 6
- Largest deal
- HelloSign ($230M)
- First deal
- 2013
- Most recent
- 2024
| Company | Year | Price | Purpose |
|---|---|---|---|
| Mailbox | 2013 | Undisclosed | Bought the gesture-based email app Mailbox; the app was shut down in 2016. |
| HelloSign | 2019 | $230.0M | Added e-signature and document workflow capabilities so users could send, sign and store agreements inside Dropbox. |
| DocSend | 2021 | $165.0M | Added secure document sharing with page-by-page viewer analytics, popular with founders, investors and sales teams. |
| FormSwift | 2022 | $95.0M | Added online templates and tools for creating, editing and signing forms. |
| Boxcryptor (assets) | 2022 | Undisclosed | Acquired encryption technology from German company Secomba to add end-to-end encryption for business teams. |
| Reclaim.ai | 2024 | Undisclosed | Added AI scheduling and calendar-management tools to support Dropbox's AI work strategy. |
- What companies has Dropbox bought?
- Major acquisitions by Dropbox documented here include HelloSign (2019), DocSend (2021), FormSwift (2022), Reclaim.ai (2024) and Boxcryptor (assets) (2022).
- What is Dropbox's most recent acquisition?
- The most recent Dropbox acquisition documented here is Reclaim.ai, in 2024.
FormSwift
2022
$95M
Why
Added online templates and tools for creating, editing and signing forms.
Outcome
Dropbox sharply cut investment in FormSwift in early 2025 and plans to wind it down by the end of 2026.
Boxcryptor (assets)
2022
Why
Acquired encryption technology from German company Secomba to add end-to-end encryption for business teams.
DocSend
2021
$165M
Why
Added secure document sharing with page-by-page viewer analytics, popular with founders, investors and sales teams.
Impact
Extended Dropbox from internal collaboration into tracked external sharing.
Outcome
Operates as part of Dropbox's workflow product family alongside Dropbox Sign.
HelloSign
2019
$230M
Why
Added e-signature and document workflow capabilities so users could send, sign and store agreements inside Dropbox.
Impact
Gave Dropbox a direct product against DocuSign and Adobe Sign and a route into higher-value business workflows.
Outcome
Rebranded as Dropbox Sign and offered as a standalone product and in bundled plans.
Mailbox
2013
Why
Bought the gesture-based email app Mailbox; the app was shut down in 2016.
Dropbox, Inc.'s Growth & Acquisition Strategy
Dropbox is trying to move from storage utility to AI-assisted workspace. It launched Dash, an AI search and answer tool across connected apps, in 2023 and is now building Dash directly into Dropbox for its 18 million-plus paying customers. Workflow add-ons came from acquisitions: HelloSign (2019, about $230 million), DocSend (2021, about $165 million) and Reclaim.ai (2024). At the same time it is pruning: it cut 528 jobs (about 20% of staff) in October 2024 and is shutting down FormSwift by the end of 2026.
How Dropbox, Inc. Makes Money
Dropbox runs a freemium subscription model. Anyone can sign up for a free Basic account with 2GB of storage; revenue comes when individuals upgrade to paid plans such as Plus, Essentials or Professional, or when teams buy per-seat Business and Business Plus plans with admin controls, more storage and security features. Add-on products, including Dropbox Sign (e-signatures), DocSend (secure document sharing with analytics) and Dash (AI search across connected apps), raise revenue per user. Sharing is the growth engine: every shared link puts Dropbox in front of a non-user. At the end of Q2 2026 Dropbox had 18.19 million paying users paying an average of $139.68 a year.
Dropbox Acquisitions FAQ
What are the most notable corporate acquisitions in Dropbox's history?
Key historical acquisitions include HelloSign / Dropbox Sign (2019 for $230 million), DocSend (2021 for $165 million), FormSwift (2022 for $95 million), and Boxcryptor key encryption assets (2022).
Why was the 2019 acquisition of HelloSign for $230 million transformative?
Acquiring HelloSign (rebranded as Dropbox Sign) gave Dropbox an immediate, leading position in digital workflow automation and legally binding e-signatures, integrating electronic contract signing natively into Dropbox folders for over 80,000 business customers.
How did the 2021 acquisition of DocSend for $165 million enhance document analytics?
Acquiring DocSend added secure document sharing and real-time page-by-page reader tracking to Dropbox's portfolio, allowing sales teams, founders, and legal professionals to manage sensitive documents and track reader engagement.
Why did Dropbox acquire FormSwift for $95 million in 2022?
Dropbox acquired FormSwift to provide users with a comprehensive template library and cloud software to create, edit, and sign legal forms, tax documents, real estate contracts, and business agreements directly inside the Dropbox ecosystem.
What technology did Dropbox acquire from Boxcryptor in 2022?
Dropbox acquired the core intellectual property and technology assets of German encryption pioneer Boxcryptor, integrating native zero-knowledge end-to-end encryption into Dropbox for business and enterprise customers.
What early mobile photo and email startups did Dropbox acquire in 2012 to 2014?
In its early years, Dropbox acquired Mailbox (popular gesture-based email app), Loom, and Snapjoy, using their mobile engineering talent and technology to build early photo management and synchronization features.
What is Dropbox's M&A philosophy under CEO Drew Houston?
Dropbox favours small acquisitions that add document workflow, security or AI capabilities, such as HelloSign, DocSend, Boxcryptor's technology and Reclaim.ai, and has pruned ones that did not fit, like FormSwift, which is being wound down by the end of 2026.
How does Dropbox integrate acquired companies into its unified subscription plans?
Dropbox integrates acquired tools directly into unified product tiers (such as the Dropbox Essentials bundle combining storage, DocSend tracking, and Dropbox Sign), driving cross-selling and higher Average Revenue Per User.
What companies has Dropbox acquired?
To avoid being just a "dumb hard drive in the cloud," Dropbox aggressively acquired workflow tools. They bought HelloSign in 2019 for $230M (to compete with DocuSign in e-signatures) and DocSend in 2021 for $165M (to dominate secure document sharing).
Related M&A Histories
Compare corporate acquisition records, deal values, and strategic targets
Explore Dropbox
Core profile pages, founders and related research hubs for this company.